I Didn't Know How to Ask for Money, Until I Had to

Growing up, I never saw anyone ask for money. As a CEO, I now don’t have a choice.

Three months ago, at the start of the Goldman Sachs One Million Black Women: Black in Business program, we were asked to bring something to orientation: a “Letter to Money.”

I wrote it honestly. From the place I was in at the time. But looking back now, with all the growth that’s happened since, there’s so much I didn’t say.

THE MINDSET I CAME IN WITH

For the past 7 years, I have helped Black women recognize what they’re worth. I can walk them through their value, their impact, and their pricing with ease.

But it hit me during the program…

No one had ever really done that for me. Not in a way that was tangible. Not with resources. Not with strategy behind it.

Growing up, I was always praised. I was the gifted kid. The one who didn’t need help. The one who got it done. I was deeply loved and supported, and because of that, I knew I was valuable.

But knowing you're valuable and believing you're worthy, especially as an adult, as a business owner, as a Black woman asking for real money, those are two different things.

Asking for money has always felt like a last resort.

Asking felt like weakness.

Like something I should only do if I couldn’t figure it out myself.

And I always figured it out myself.

That’s the praise I was raised on. That’s the skillset I mastered. But in business, that mindset doesn’t work.

Because while I always felt worthy growing up, the version of worth I knew then isn’t the kind you need when you’re running a business. Especially when you’re trying to scale one.

As a founder, you don’t get a gold star for showing up. You don’t get praised for making payroll. There’s no applause when you figure out how to pay the invoice and still manage daycare tuition. The worth you carry has to come from within, and it has to be sustained by systems, not sentiment.

THE PART I DIDN’T WRITE IN THE LETTER

If I rewrote that letter to money today, I’d say a lot of the same things. But I’d also say more.

I’d talk about how I’m relaunching The Influencer League, building Gage, and mapping out a five-to-seven-year vision to close the influencer pay gap.

I’d talk about how, in order to do that, we need more money. Not eventually, but now.

Revenue is coming in. Systems are being built. But to scale sustainably, we need more cash flow upfront. We need a few more team members (I still want a lean, mean team), expanded infrastructure, and more resources.

Which means: I have to ask for it.

WHY ASKING FOR MONEY HAS BEEN HARD

That’s where the reframe really began.

Because I realized: I’ve never liked asking for money. I hate it. And not in the cute, humble-brag way. I deeply dislike it. If I’m struggling, no one’s going to know. I’m going to figure it out behind closed doors.

Growing up, I never saw my mom ask for help. I never saw the financial struggle. Everything was quiet, held close, and done with grace. And even if something cost her a lot, my siblings and I still had what we needed and even what we wanted.

So now, as an adult, I mirror that same pattern. I work hard. I stretch every dollar. I budget and manage cash flow. I make it look effortless, even when it’s not.

But that mentality won’t take you far at this level. Not as a CEO. Not as a founder trying to raise capital.

At some point, hiding the ask starts holding back the mission.

THE MINDSET I’M STEPPING INTO

I’m not ashamed of where I come from. I’m proud of how I was raised. But I also know: I’m building something my family has never seen before. And that means asking for amounts of money we’ve never touched before.

The shift is this: I’m no longer afraid to be visible in the ask.

Because what I’m building is bigger than my discomfort. It’s bigger than my pride, AND it’s bigger than me.

The past few months in the program have completely shifted the way I see myself, what I deserve, and how money moves toward me when I’m clear. Not perfect. Not prepared within an inch of my life. Just clear.

I had to sit with the fact that no one ever showed me what I was worth in tangible ways, through investment, support, or access. I had to unlearn the instinct to make do in every situation. And I had to confront the reality that even with all my knowledge, all my experience, and all my receipts… asking still made me feel exposed.

Here’s what I’m just now starting to unpack.

Negotiating is familiar to me. It’s structured. Strategic.

There’s already an offer on the table, and I’m just making sure it reflects my value.

But asking, especially when it comes to sales, loans, or funding, feels different.

It feels exposed. There’s no starting point. No script.

Just me, believing I’m worthy of the thing I’m asking for.

And that’s what I’m working through.

Because it’s not about confidence. It’s about conditioning.

I was raised to be excellent, to figure it out, to make do. Not to say, “I need this.” Not to lead with the ask.

That’s the real work now. Not just knowing my worth, but feeling safe enough to ask for what reflects it.

REFLECTING BACK ON THE LETTER

So if I could go back and rewrite that letter to money, I’d still thank it. I’d still respect it. But I’d also name what I need, boldly and without apology.

Because I’m no longer just working for money. I’m working with it toward something bigger, sustainable, and long-lasting.

And I’m willing to ask for what that takes.

If you’re a Black woman founder reading this, I hope you give yourself permission to ask. Not just because you’ve earned it, but because the mission needs it.

Be Bright,

Brittany